Synthetic or model receptors for biorelevant targets are proposed as a means of evaluating intermolecular forces. The systems involve the use of U-shaped molecular modules which are combined with appropriate spacer elements to provide cleft-like concave structures. These feature convergent functional groups, complementary to the convex surfaces of the targets. Peripheral functions provide a range of solubilities for determination of hydrogen bonding, stacking and van der Waals forces in a variety of solvents. Target structure include heterocyclics, amino acids, peptides and metal ions. Asymmetric microenvironments are also proposed for enantioselective recognition and the control for stereochemistry.